HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 68505802, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 86622960 | HCID 86622960 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 68505802 | HCID 68505802 | 65.2% |
Reaction Steps
A mixture of N-[2-(4-chloro-3-formyl-phenyl)-ethyl]-3,3,3-trifluoro-propionamide (175 mg, 0.596 mmol), Et3N (0.125 mL, 0.896 mmol) and cyclopropylamine (0.063 mL, 0.90 mmol) in MeOH (2.00 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (56.4 mg, 1.49 mmol) was added in portions. The mixture was stirred for 1 h, and aq. sat. NaHCO3 was added. The mixture was extracted with EtOAc several times, and the combined org. extracts were washed with brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (CH2Cl2/MeOH 95:5) yielded the title compound (130 mg, 65%). LC-MS: tR=0.65 min; ES+: 335.12.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07799805B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-a03d663cf42c40258f350b6caf27204a |
| Source note | uspto-grants-2010_09 |